#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:48:20 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178445 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/66/4026606.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4026606
loop_
_publ_author_name
'Goutam Kumar Kole'
'Geok Kheng Tan'
'Jagadese J. Vittal'
_publ_contact_author
; 
     Dr. Jagadese J. Vittal
     Department of Chemistry
     National University of Singapore
     3 Science Drive 3
     SINGAPORE 117543 
;
_publ_contact_author_email       chmjjv@nus.edu.sg
_publ_contact_author_fax         '(65) 6779 1691'
_publ_contact_author_phone       '(65) 6516 2677'
_publ_section_title
;
 Role of Anions in the Synthesis of Cyclobutane Derivatives via [2 + 2]
 Cycloaddition Reaction in the Solid State and Their Isomerization in
 Solution
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              7860
_journal_page_last               7865
_journal_paper_doi               10.1021/jo201268p
_journal_volume                  76
_journal_year                    2011
_chemical_formula_sum            'C16 H14 N2 O4'
_chemical_formula_weight         298.29
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           9
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 118.305(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.723(2)
_cell_length_b                   9.6367(14)
_cell_length_c                   10.5485(16)
_cell_measurement_reflns_used    2097
_cell_measurement_temperature    223(2)
_cell_measurement_theta_max      27.44
_cell_measurement_theta_min      2.63
_cell_volume                     1317.7(3)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      223(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0445
_diffrn_reflns_av_sigmaI/netI    0.0620
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            3927
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.63
_exptl_absorpt_coefficient_mu    0.110
_exptl_absorpt_correction_T_max  0.9934
_exptl_absorpt_correction_T_min  0.9532
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2005)'
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_density_diffrn    1.504
_exptl_crystal_density_meas      ?
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.06
_refine_diff_density_max         1.474
_refine_diff_density_min         -0.620
_refine_diff_density_rms         0.225
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -2(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.666
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         1997
_refine_ls_number_restraints     98
_refine_ls_restrained_S_all      1.666
_refine_ls_R_factor_all          0.1417
_refine_ls_R_factor_gt           0.1405
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.2000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3440
_refine_ls_wR_factor_ref         0.3471
_reflns_number_gt                1939
_reflns_number_total             1997
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo201268p_si_002_1.cif
_cod_data_source_block           compound_4
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'Not Measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_database_code               4026606
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z+1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
N1 N -0.0407(5) -0.0124(5) 0.7274(7) 0.0422(17) Uani 1 1 d .
N2 N 0.2979(6) -0.0067(6) 1.0862(7) 0.0449(18) Uani 1 1 d .
O1 O 0.0301(5) 0.6728(7) 0.6595(6) 0.0495(16) Uani 1 1 d .
O2 O -0.0098(5) 0.7252(5) 0.8325(6) 0.0457(16) Uani 1 1 d .
H2 H -0.0309 0.7980 0.7856 0.069 Uiso 1 1 calc R
O3 O 0.2448(4) 0.7195(6) 1.0989(5) 0.0405(14) Uani 1 1 d .
H3 H 0.2757 0.7938 1.1073 0.061 Uiso 1 1 calc R
O4 O 0.2741(5) 0.6865(7) 0.9130(6) 0.0526(17) Uani 1 1 d .
C1 C 0.0899(5) 0.3937(6) 0.7747(6) 0.0240(14) Uani 1 1 d U
H1 H 0.0829 0.4254 0.6812 0.029 Uiso 1 1 calc R
C2 C 0.2073(5) 0.3952(6) 0.8948(6) 0.0244(13) Uani 1 1 d U
H2A H 0.2532 0.4272 0.8562 0.029 Uiso 1 1 calc R
C3 C 0.1820(6) 0.5135(7) 0.9730(7) 0.0320(15) Uani 1 1 d U
H3A H 0.1890 0.4814 1.0663 0.038 Uiso 1 1 calc R
C4 C 0.0648(6) 0.5141(7) 0.8518(7) 0.0301(15) Uani 1 1 d U
H4 H 0.0190 0.4820 0.8906 0.036 Uiso 1 1 calc R
C5 C 0.2400(5) 0.6505(6) 0.9901(6) 0.0232(13) Uani 1 1 d U
C6 C 0.0269(5) 0.6457(6) 0.7712(6) 0.0226(12) Uani 1 1 d U
C11 C 0.0321(6) 0.2577(6) 0.7566(8) 0.0357(18) Uani 1 1 d U
C12 C 0.0524(6) 0.1585(10) 0.6735(7) 0.045(2) Uani 1 1 d U
H12 H 0.0919 0.1816 0.6279 0.054 Uiso 1 1 calc R
C13 C 0.0128(7) 0.0294(9) 0.6624(8) 0.044(2) Uani 1 1 d U
H13 H 0.0240 -0.0353 0.6045 0.053 Uiso 1 1 calc R
C14 C -0.0595(6) 0.0776(8) 0.7991(7) 0.0364(16) Uani 1 1 d U
H14 H -0.0985 0.0493 0.8439 0.044 Uiso 1 1 calc R
C15 C -0.0272(5) 0.2149(7) 0.8168(6) 0.0296(15) Uani 1 1 d U
H15 H -0.0458 0.2772 0.8692 0.035 Uiso 1 1 calc R
C16 C 0.2454(6) 0.2579(6) 0.9795(7) 0.0315(16) Uani 1 1 d U
C17 C 0.2201(5) 0.2090(8) 1.0807(7) 0.0322(16) Uani 1 1 d U
H17 H 0.1872 0.2656 1.1192 0.039 Uiso 1 1 calc R
C18 C 0.2450(7) 0.0733(10) 1.1232(9) 0.0437(19) Uani 1 1 d U
H18 H 0.2213 0.0362 1.1846 0.052 Uiso 1 1 calc R
C19 C 0.3273(7) 0.0453(9) 0.9919(8) 0.048(2) Uani 1 1 d U
H19 H 0.3660 -0.0109 0.9622 0.058 Uiso 1 1 calc R
C20 C 0.3026(6) 0.1760(10) 0.9393(8) 0.0407(18) Uani 1 1 d U
H20 H 0.3249 0.2100 0.8752 0.049 Uiso 1 1 calc R
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C14 N1 C13 116.9(6)
C18 N2 C19 116.9(6)
C11 C1 C4 116.7(6)
C11 C1 C2 116.1(5)
C4 C1 C2 90.8(5)
C16 C2 C3 115.8(5)
C16 C2 C1 114.4(5)
C3 C2 C1 89.2(5)
C5 C3 C2 115.7(6)
C5 C3 C4 115.0(5)
C2 C3 C4 91.0(5)
C6 C4 C1 117.1(5)
C6 C4 C3 115.8(6)
C1 C4 C3 88.9(5)
O4 C5 O3 126.1(7)
O4 C5 C3 124.1(6)
O3 C5 C3 109.7(5)
O1 C6 O2 125.2(6)
O1 C6 C4 123.9(6)
O2 C6 C4 111.0(5)
C15 C11 C12 116.9(6)
C15 C11 C1 130.1(7)
C12 C11 C1 112.8(7)
C13 C12 C11 117.6(7)
N1 C13 C12 124.7(6)
N1 C14 C15 125.1(6)
C11 C15 C14 118.7(6)
C20 C16 C17 118.7(6)
C20 C16 C2 115.2(7)
C17 C16 C2 125.9(7)
C16 C17 C18 116.9(6)
N2 C18 C17 125.5(6)
C20 C19 N2 121.8(7)
C19 C20 C16 119.9(7)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C14 1.266(11)
N1 C13 1.328(12)
N2 C18 1.281(12)
N2 C19 1.355(13)
O1 C6 1.229(9)
O2 C6 1.276(8)
O3 C5 1.300(7)
O4 C5 1.191(8)
C1 C11 1.524(8)
C1 C4 1.559(8)
C1 C2 1.586(9)
C2 C16 1.545(8)
C2 C3 1.551(9)
C3 C5 1.536(9)
C3 C4 1.588(10)
C4 C6 1.481(9)
C11 C15 1.365(11)
C11 C12 1.422(12)
C12 C13 1.355(13)
C14 C15 1.388(10)
C16 C20 1.360(12)
C16 C17 1.370(11)
C17 C18 1.374(12)
C19 C20 1.355(13)
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2 H2 N1 0.83 1.91 2.712(8) 161.9 1_565
O3 H3 N2 0.83 1.98 2.773(8) 159.5 1_565
